EP1474460B1 - Prepolymeres polyurethannes a fonctionnalite reduite, contenant des groupes terminaux alcoxysilanes et oh, procede de production et utilisation desdits prepolymeres - Google Patents

Prepolymeres polyurethannes a fonctionnalite reduite, contenant des groupes terminaux alcoxysilanes et oh, procede de production et utilisation desdits prepolymeres Download PDF

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Publication number
EP1474460B1
EP1474460B1 EP03737273A EP03737273A EP1474460B1 EP 1474460 B1 EP1474460 B1 EP 1474460B1 EP 03737273 A EP03737273 A EP 03737273A EP 03737273 A EP03737273 A EP 03737273A EP 1474460 B1 EP1474460 B1 EP 1474460B1
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Prior art keywords
groups
polyurethane prepolymers
radicals
alkoxysilane
polyurethane
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EP1474460A1 (fr
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Michael Ludewig
Mathias Matner
Stefan Groth
Gerhard Ruttmann
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Covestro Deutschland AG
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Bayer MaterialScience AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1021—Polyurethanes or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step

Definitions

  • the invention relates to alkoxysilane and OH-terminated polyurethane prepolymers based on high molecular weight polyurethane prepolymers having reduced functionality, a process for their preparation by premature termination of the synthesis reaction and their use as binders for low-modulus sealants and adhesives.
  • Alkoxysilane-functional polyurethanes which crosslink via a silane polycondensation have long been known. A review on this topic can be found eg in " Adhesives Age "4/1995, page 30 ff. (Authors: Ta-Min Feng, BA Waldmann ). Such alkoxysilane-terminated, moisture-curing, one-component polyurethanes are increasingly being used as soft-elastic coating, sealing and adhesive compounds in construction and in the automotive industry. In these applications, high demands are placed on the elongation, adhesion and curing speed. However, in particular the property level required in the construction sector could not be fully achieved by these systems.
  • a usable as a building sealant alkoxysilyl-functional polyurethane prepolymer is described in the WO 00/26271 described.
  • a high molecular weight polypropylene oxide polyether prepared by double metal cyanide catalysis is used as the basis, which guarantees a relatively low viscosity in the prepolymer synthesis in combination with the use of secondary aminosilanes.
  • Such compounds have at a (calculated from NCO and functionality) average molecular weights of more than 15,000 g / mol quite a suitable property profile in order to be used as sealants.
  • the viscosities of such systems are quite high, which limits their applicability considerably.
  • the DE-A 3629237 describes an alkoxysilyl-functional polyurethane system which achieves better elasticity by reducing functionality. This is achieved by subsequently reducing functionality either with monoalcohols or through the use of monoisocyanates. However, the property level of a construction sealant is not achieved in this way.
  • Prepolymers have also become known which basically contain alkoxysilane and OH end groups.
  • DE-A 3 220 865 will be based on a pressure-sensitive adhesive such compounds described.
  • This DE-A describes the synthesis with adducts of diisocyanate and aminosilanes, which, however, involves the disadvantage of a two-stage synthesis.
  • the diadduct of two molecules aminosilane and diisocyanate will form, expensive aminosilane is lost and produces a higher hardness, which is undesirable in the sealant area.
  • the object of the present invention was therefore to provide alkoxysilane-terminated polyurethane prepolymers which overcome the disadvantages set forth in the prior art. This object has been achieved by providing the polyurethane prepolymers having alkoxysilane and OH end groups described in more detail below based on high molecular weight polyurethane prepolymers.
  • X, Y and Z are independently methoxy or ethoxy; for R ', a radical of the general formula (II) is preferred.
  • the lowering of the functionality of the prepolymers of the invention results in a lower modulus polymer.
  • prepolymers of relatively low average molecular weight and low viscosity can be used to achieve a high level of properties.
  • the prepolymer according to the invention achieves this profile by incomplete reaction of the OH groups of the polyethers used with a diisocyanate and subsequent termination of the terminal NCO groups by aminosilanes. It was surprisingly found that the remaining OH groups do not lead to a reduction in storage stability and also do not interfere with curing in the polymerization process.
  • the isocyanate prepolymers A) to be used according to the invention are prepared in the manner known per se from polyurethane chemistry by reacting a diisocyanate component i) with a polyol component ii) which is characterized in more detail below.
  • polyisocyanate component i) isocyanates which can be used according to the invention are any aliphatic, cycloaliphatic or aromatic diisocyanates of the prior art with an isocyanate content of from 20 to 60% by weight.
  • aromatic or cycloaliphatic diisocyanates are meant those having at least one aromatic or cycloaliphatic ring per molecule, preferably but not necessarily, at least one of the two isocyanate groups is directly linked to an aromatic or cycloaliphatic ring .
  • component i) or part of component i) are preferably suitable aromatic or cycloaliphatic diisocyanates of molecular weight range 174 to 300 such as 4,4'-diphenylmethane diisocyanate, optionally in admixture with 2,4'-diphenylmethane diisocyanate, 2,4-diisocyanatotoluene whose technical mixtures preferably with up to 35% by weight, based on the mixture, of
  • Particularly preferred component i) is 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI).
  • the diisocyanate component i) is reacted with a polyol component ii) such that 10 to 50% of the OH groups of the polyol component ii) are not reacted with the NCO groups of the diisocyanate component i), so that in the produced polyurethane prepolymer A) 50 to 90% of the OH groups of the polyol component ii) are reacted.
  • the polyol component ii) contains a polyoxyalkylene diol having a molecular weight of 3,000 to 20,000 (corresponding to an OH number of 37.3 to 5.6), preferably 4000 to 15000 (corresponding to an OH number of 28 to 7.5). having.
  • the polyoxyalkylene diols which can preferably be used according to the invention can be prepared in a manner known per se from polyurethane chemistry by ethoxylation and / or propoxylation of suitable starter molecules.
  • suitable starter molecules are diols, such as ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 2-ethylhexanediol-1,3 or primary monoamines, for example aliphatic amines, such as ethylamine or butylamine.
  • Preferred polyoxyalkylene diols have an average molecular weight calculated from OH content and functionality of from 3,000 to 20,000, preferably from 4,000 to 15,000, and an ethylene oxide content of not more than 20% by weight, based on the total weight of the polyoxyalkylene diol.
  • polypropylene oxide polyethers having a terminal unsaturation of not more than 0.04 meq / g and a mean molecular weight of 8000 to 12000 calculated from OH content and functionality.
  • polyether polyols having a low degree of unsaturation which are particularly preferably usable according to the invention are known in principle and are described by way of example in US Pat EP-A 283 148 .
  • US-A 3,278,457 are known in principle and are described by way of example in US Pat EP-A 283 148 .
  • NCO prepolymers A may optionally minor amounts of low molecular weight 2 and 3-valent alcohols of molecular weight 32 to 500 are used.
  • low molecular weight 2 and 3-valent alcohols include ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, glycerol or trimethylolpropane.
  • the concomitant use of low molecular weight alcohols is by no means preferred.
  • the polyurethane prepolymers which can be used according to the invention as component A) are prepared by reacting the diisocyanate component i) with the diol component ii) in the temperature range from 40 to 120 ° C., preferably 50 to 100 ° C., while maintaining an NCO / OH equivalent ratio of 1.2 : 1 to 2.0: 1, preferably 1.3: 1 to 1.8: 1.
  • the reaction is stopped as soon as a conversion of 50-90% of the OH groups of the polyol component, preferably 70-85% of the OH groups of the polyol component, has been achieved, ie the polyol component still 10 to 50%, preferably 30 to 15% free , does not contain OH groups reacted with NCO groups.
  • the conversion is determined by an NCO titrimetric method customary in polyurethane chemistry.
  • the reaction is stopped by the addition of a small amount of a mineral or organic acid such as hydrochloric acid, sulfuric acid, phosphoric acid or its derivatives, formic acid, acetic acid or other alkane or organic acid or an acid releasing component such as acid halides.
  • a mineral or organic acid such as hydrochloric acid, sulfuric acid, phosphoric acid or its derivatives
  • formic acid acetic acid or other alkane or organic acid or an acid releasing component such as acid halides.
  • exemplary here are formic acid chloride, acetic acid chloride, propionic acid chloride and benzoyl chloride.
  • the use of the stopper can be dispensed with and the aminosilane compound can be added directly. It is necessary to proceed quickly in order to prevent the further progress of the isocyanate-OH reaction to the detriment of the isocyanate-NH reaction as far as possible.
  • polyurethane prepolymers known from polyurethane chemistry per se amine or organometallic catalysts can be used.
  • dibutyltin dilaurate is added as a catalyst using isophorone diisocyanate.
  • the inventively employable polyurethane prepolymers A) have an NCO content of 0.1 to 2.6%, preferably 0.3 to 2.0%. Depending on the ratio of NCO to OH groups, this corresponds to an average molecular weight of 3,000 to 42,000, preferably 4,000 to 20,000.
  • the reaction of the NCO prepolymers with the compounds of the formula (I) containing alkoxysilane and amino groups in the process according to the invention takes place within a temperature range from 0 to 150 ° C., preferably 20-80 ° C., the proportions generally being chosen such that that 0.95 to 1.1 mol of aminosilane compound are used per mole of NCO groups used. Preferably, 1 mole of aminosilane compound is used per mole of NCO groups used.
  • Another object of the invention is the use of the invention alkoxysilane and OH-terminated polyurethane prepolymers as a binder for the preparation of isocyanate-free low modulus polyurethane sealants preferably for the construction sector.
  • sealants crosslink under the action of atmospheric moisture via a silanol polycondensation. Furthermore, they are suitable for the production of adhesives; an application in primers or coatings is also conceivable.
  • Another object of the invention are sealants, adhesives, primers and coatings based on the inventive alkoxysilane and OH-terminated polyurethane prepolymers.
  • the polyurethane prepolymers of the invention containing alkoxysilane end groups can be formulated together with customary plasticizers, fillers, pigments, drying agents, additives, light stabilizers, antioxidants, thixotropic agents, catalysts, adhesion promoters and, if appropriate, other auxiliaries and additives according to known methods of sealant production.
  • suitable fillers are carbon black, precipitated silicas, pyrogenic silicic acids, mineral chalks and precipitation precipitates.
  • suitable plasticizers include phthalic acid esters, adipic acid esters, alkylsulfonic acid esters of phenol or phosphoric acid esters.
  • thixotropic agents examples include pyrogenic silicic acids, polyamides, hydrogenated castor oil derived products or else polyvinyl chloride.
  • Suitable catalysts for curing are organotin compounds and amine catalysts.
  • organotin compounds may be mentioned by way of example: dibutyltin diacetate, dibutyltin dilaurate, dibutyltin bis-acetoacetonate and tin carboxylates such as tin octoate.
  • the said tin catalysts may optionally be used in combination with amine catalysts such as aminosilanes or diazabicyclooctane.
  • drying agents are alkoxysilyl compounds such as vinyltrimethoxysilane, methyltrimethoxysilane, i-butyltrimethoxysilane, hexadecyltrimethoxysilane.
  • Adhesion promoters used are the known functional silanes, for example aminosilanes of the abovementioned type, but also N-aminoethyl-3-aminopropyltrimethoxy and / or N-aminoethyl-3-aminopropylmethyldimethoxysilane, epoxysilanes and / or mercaptosilanes.
  • the crosslinked polymers are characterized by excellent extensibility combined with low modulus. With a decreasing NCO / OH ratio at the same molecular weight of the polymer, a decrease in the modulus and the Shore hardness as well as an increase in the elongation at break are observed. The increase in surface tack is only slight in the preferred range of the invention.
  • the mixture is dispersed for 15 minutes at a pressure of 100 mbar, wherein the internal temperature rises to 60 ° C. Subsequently, under cooling 4.5 g Dynasilan® ® DAMO (Degussa AG, Frankfurt a. M.) added and incorporated at a pressure of 100 mbar by stirring for 5 minutes. Then be 4.5 g Tegokat 233 ® (10% in DIDP) (Goldschmidt AG, Essen) added and stirred for 10 minutes at 100mbar.
  • Dynasilan® ® DAMO Degussa AG, Frankfurt a. M.
  • the sealant thus produced shows the following property profile: Skin formation (25 ° C / 45% rh) 45min Shore A 37 tensile strenght 2.8 N / mm 2 100% modulus 1.1 N / mm 2 elongation at break 336% Tear strength 13.1 N / mm
  • the sealant shows a low surface tack and a good storage stability.
  • the mixture is dispersed for 15 minutes at a pressure of 100 mbar, wherein the internal temperature rises to 60 ° C. Subsequently, under cooling 4.5 g Dynasilan® ® DAMO (Degussa AG, Frankfurt a. M.) added and incorporated at a pressure of 100 mbar by stirring for 5 minutes. Then be 4.5 g Tegokat 233 ® (10% in DIDP) (Goldschmidt AG, Essen) added and stirred for 10 minutes at 100mbar.
  • Dynasilan® ® DAMO Degussa AG, Frankfurt a. M.
  • the sealant thus produced shows the following property profile: Skin formation (25 ° C / 45% rh) 35min Shore A 45 tensile strenght 3.3 N / mm 2 100% modulus 1.4 N / mm 2 elongation at break 343% Tear strength 12.2 N / mm
  • the sealant shows a low surface tack and a good storage stability.
  • the mixture is dispersed for 15 minutes at a pressure of 100 mbar, wherein the internal temperature rises to 60 ° C. Subsequently, under cooling 4.5 g Dynasilan® ® DAMO (Degussa AG, Frankfurt a. M.) added and incorporated at a pressure of 100 mbar by stirring for 5 minutes. Then be 4.5 g Tegokat 233 ® (10% in DIDP) (Goldschmidt AG, Essen) added and stirred for 10 minutes at 100mbar.
  • Dynasilan® ® DAMO Degussa AG, Frankfurt a. M.
  • the sealant thus produced shows the following property profile: Skin formation (25 ° C / 45% rh) 15 minutes Shore A 52 tensile strenght 3.7 N / mm 2 100% modulus 1.7 N / mm 2 elongation at break 363% Tear strength 9.0 N / mm
  • the sealant shows a very low surface tack and a good storage stability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Sealing Material Composition (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)

Claims (13)

  1. Prépolymères de polyuréthane présentant des groupes terminaux alcoxysilane et OH pouvant être obtenus en faisant réagir
    A) des prépolymères de polyuréthane préparés par une réaction incomplète, stoppée après la conversion de 50 à 90 % des groupes OH du composant polyol,
    i) d'un composant diisocyanate aromatique, aliphatique ou cycloaliphatique ayant une teneur en NCO de 20 à 60% en poids avec
    ii) un composant polyol constitué d'un polyoxyalkylène diol ayant une masse moléculaire dans la plage de 3 000 à 20 000,
    avec
    B) des composés présentant des groupes alcoxysilane et amino de formule (I)
    Figure imgb0013
     dans laquelle
    X, Y, Z représentent des restes alkyle en C1 à C8 ou alkoxy en C1 à C8 identiques ou différents et le cas échéant ramifiés, à la condition que l'un au moins de ccs restes soit un groupe alcoxy en C1 à C8,
    R représente des radicaux alkylène de à 8 atomes de carbone, le cas échéant ramifiés,
    R' représente l'hydrogène, des restes alkyle en C1 à C8, des restes aryle en C6 à C10 ou des restes de formule générale (II)
    Figure imgb0014
     dans laquelle
    R" et R"' sont des restes alkyle de 1 à 8 atomes de carbone, identiques ou différents et le cas échéant ramifiés.
  2. Prépolymères de polyuréthane présentant des groupes terminaux alcoxysilane et OH selon la revendication 1, caractérisés en ce que le composant polyuréthane A) est préparé par une réaction incomplète de i) et ii), stoppée après la conversion de 70 à 85% des groupes OH du composant polyol.
  3. Prépolymères de polyuréthane présentant des groupes terminaux alcoxysilane et OH selon la revendication 1, caractérisés en ce que l'on utilise pour préparer les prépolymères de polyuréthane A) des polyéthers de polyoxyde de propylène ayant une insaturation terminale de 0,04 méq/g au maximum et une masse moléculaire moyenne, calculée à partir de la teneur en OH et de la fonctionnalité, dans la plage de 3 000 à 20 000.
  4. Prépolymères de polyuréthane présentant des groupes terminaux alcoxysilane et OH selon la revendication 1, caractérisés en ce que le reste R' est un reste de formule générale (II).
  5. Prépolymères de polyuréthane présentant des groupes terminaux alcoxysilane et OH selon la revendication 1, caractérisés en ce que X, Y et Z représentent indépendamment les uns des autres des groupes méthoxy ou éthoxy.
  6. Procédé de production de prépolymères de polyuréthane présentant des groupes terminaux alcoxysilane et OH selon les revendications 1 à 5, qui consiste à faire réagir
    A) des prépolymères de polyuréthane préparés par une réaction incomplète, stoppée après la conversion de 50 à 90 % des groupes OH du composant polyol,
    i) d'un composant diisocyanate aromatique, aliphatique ou cycloaliphatique ayant une teneur en NCO de 20 à 60% en poids avec
    ii) un composant polyol constitué d'un polyoxyalkylène diol ayant une masse moléculaire dans la plage de 3 000 à 20 000,
    avec
    B) des composés présentant des groupes alcoxysilane et amino de formule (I)
    Figure imgb0015
    dans laquelle
    X, Y, Z représentent des restes alkyle en C1 à C8 ou alcoxy en C1 à C8 identiques ou différents et le cas échéant ramifiés, à la condition que l'un au moins de ces restes soit un groupe alcoxy en C1 à C8,
    R représente des radicaux alkylène de à 8 atomes de carbone, le cas échéant ramifiés,
    R' représente l'hydrogène, des restes alkyle en C1 à C8, des restes aryle en C6 à C10 ou des restes de formule générale (II)
    Figure imgb0016
     dans laquelle
    R" et R"' sont des restes alkyle de 1 à 8 atomes de carbone, identiques ou différents et le cas échéant ramifiés.
  7. Utilisation des prépolymères de polyuréthane selon la revendication 1 comme liants pour fabriquer des produits d'étanchéité, des adhésifs, des mastics et des,revêtements à faible module.
  8. Produits d'étanchéité à base des prépolymères de polyuréthane selon la revendication 1.
  9. Adhésifs à base des prépolymères de polyuréthane selon la revendication 1.
  10. Mastics et revêtements à base des prépolymères de polyuréthane selon la revendication 1.
  11. Substrats étanchéifiés avec des produits d'étanchéité selon la revendication 8.
  12. Substrats encollés avec des adhésifs selon la revendication 9.
  13. Substrats mastiqués ou revêtus avec des mastics ou des revêtements selon la revendication 10.
EP03737273A 2002-02-05 2003-01-24 Prepolymeres polyurethannes a fonctionnalite reduite, contenant des groupes terminaux alcoxysilanes et oh, procede de production et utilisation desdits prepolymeres Expired - Lifetime EP1474460B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10204523A DE10204523A1 (de) 2002-02-05 2002-02-05 Alkoxysilan- und OH-Endgruppen aufweisende Polyurethanprepolymere mit erniedrigter Funktionalität, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE10204523 2002-02-05
PCT/EP2003/000760 WO2003066701A1 (fr) 2002-02-05 2003-01-24 Prepolymeres polyurethannes a fonctionnalite reduite, contenant des groupes terminaux alcoxysilanes et oh, procede de production et utilisation desdits prepolymeres

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EP1474460A1 EP1474460A1 (fr) 2004-11-10
EP1474460B1 true EP1474460B1 (fr) 2009-01-07

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US (1) US6762270B2 (fr)
EP (1) EP1474460B1 (fr)
JP (1) JP4171424B2 (fr)
CN (1) CN1290891C (fr)
AT (1) ATE420126T1 (fr)
AU (1) AU2003244436A1 (fr)
BR (1) BR0307419A (fr)
CA (1) CA2474953C (fr)
DE (2) DE10204523A1 (fr)
DK (1) DK1474460T3 (fr)
ES (1) ES2318142T3 (fr)
HK (1) HK1079537A1 (fr)
MY (1) MY122976A (fr)
PT (1) PT1474460E (fr)
TW (1) TWI300070B (fr)
WO (1) WO2003066701A1 (fr)

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US20030153712A1 (en) 2003-08-14
CA2474953C (fr) 2011-03-15
TWI300070B (en) 2008-08-21
BR0307419A (pt) 2005-01-04
CN1290891C (zh) 2006-12-20
DE50311047D1 (de) 2009-02-26
JP4171424B2 (ja) 2008-10-22
ES2318142T3 (es) 2009-05-01
PT1474460E (pt) 2009-03-09
ATE420126T1 (de) 2009-01-15
WO2003066701A1 (fr) 2003-08-14
DE10204523A1 (de) 2003-08-07
TW200306990A (en) 2003-12-01
MY122976A (en) 2006-05-31
EP1474460A1 (fr) 2004-11-10
JP2005517059A (ja) 2005-06-09
HK1079537A1 (en) 2006-04-07
AU2003244436A1 (en) 2003-09-02
US6762270B2 (en) 2004-07-13
CN1628137A (zh) 2005-06-15
CA2474953A1 (fr) 2003-08-14
DK1474460T3 (da) 2009-04-20

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